“This is of my older sister, perfect in all pictures, and older brother’s gigantically chubby head. The photographer thought this was the best picture of the whole shoot. My mom thought it was hilarious and horrifying, so of course she bought it to add to the awkward family photos we had for years to come.”

“This photo has it all when it comes to awkward engagement photos. My husband and I were 19 at the time of the photo and I was still a bit rebellious. My dad was paying for the wedding (including the engagement photos) and I seized the opportunity to show him how grown up I was. I was attempting an artistic Garden of Eden which even included my pet python, Merlin. I frantically purchased fake flowers the day of the photo shoot because I was inspired to make the photo more authentic. After our traditional engagement photos, we took our clothes off and tried some alternate poses. When we got our proofs back, we showed them to my family at my birthday dinner. My grandma screamed, “OH MY GOD!” and I started crying and ran to the car where soon-to-be husband yelled, “Well, what did you expect!?!”